


Totally a Chick Flick Moment

by Artsortment



Category: Supernatural
Genre: Big Brother Dean, Cis girl!Sam, Family, Female Sam Winchester, Gen, Genderbending, High School, Rule 63, girl!Sam
Language: English
Status: Completed
Published: 2013-05-28
Updated: 2013-05-28
Packaged: 2017-12-13 04:57:51
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,757
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/820264
Author URL: https://archiveofourown.org/users/Artsortment/pseuds/Artsortment
Summary: <blockquote class="userstuff">
              <p>Sam just wants to do something normal for once in her life and go to her senior prom. But according to John, that's just too much to ask. Fortunately, Dean is the best big brother ever. (Sam is 17 and a girl. Dean is roughly 21. Rating is for mild swearing.)</p>
            </blockquote>





	Totally a Chick Flick Moment

**Author's Note:**

  * For [Transinboots](https://archiveofourown.org/gifts?recipient=Transinboots).



> Inspired by that one time I did makeup for my friend who cosplays as the Sam to my Dean.

"No Sam, and that's final!" John Winchester bellowed at his daughter, who clenched her jaw and stormed out of the motel room in lieu of a reply. Dean was pulling into the parking lot when he saw a miserable looking Sam come out of the room and sighed, knowing the signs of a Sam vs John clash all too well. He made a show of searching through the bags next to him and swearing loudly before leaning out the window. "Sammy! Get over here! I forgot something and don't feel like driving an hour by myself again."

Sam rolled her eyes and scrubbed at her face as she walked over to the car. "I swear to god Dean." She slid into the passenger seat, luxuriating in the extra leg room she got to enjoy when not relegated to the back seat. It was one of her favorite things about driving with Dean.

They drove in silence, Led Zepplin providing enough of a distraction so they didn't need to talk.

Eventually, Sam sighed and looked at Dean. "Aren't you gonna ask what happened?"

"Hm?"

"Oh come on Dean. I know you didn't actually forget anything. So friggin ask already."

Dean glared at Sam. "Bitch."

"Jerk" Sam retorted, but her mouth twitched a small smile at the comfortable routine.

Dean sighed and turned his gaze back to the road. "You tell him about Stanford?"

Sam's eyes widened, "How did you... Did you go through my stuff! You ass! How many times do I have to…"

"I'm real proud of you Sam." Dean's statement stopped Sam mid-tyrade.

"Really? You're not pissed that I'll be leaving." Sam looked skeptical.

Dean shook his head. "You're not meant for this life Sammy, and a full ride is nothing to sneeze at. Besides, pretty girls shouldn't be hunting anyway." He grinned at her.

Sam huffed. "Oh my god! You are such a sexist! Girls can hunt just as well as boys!"

"Doesn't mean they should." Sam threw up her arms in frustration at the old argument. Dean had been against Sam hunting since John decreed her old enough to withstand a gun’s kickback.

"But seriously. You did good."

She smiled. "Thanks Dean."

"So what was the fight about then?"

"Prom" Sam admitted, clearly embarrassed.

Dean almost choked. "What?"

"I asked Dad if I could go to prom. I was gonna meet Amy at the mall in an hour to go shopping for dresses. You know, be a normal teenage girl for once. Anyway, he yelled at me about the money for a while and told me no. Not that I wasn't expecting it. I even told Amy I probably wouldn't buy anything... Still, I'd hoped he'd be a normal Dad for once and be excited rather than furious." Sam looked dejected and played with a tear in her hoodie.

"So go shopping. I'll drive." Dean said. "If Amy's cool with you just looking, it doesn't hurt anything. Besides, you might have fun."

Sam's eyes lit up. "What about Dad?"

Dean shrugged. "I'll tell him I took you to the library so you could be a gigantic nerd where you wouldn't infect the rest of us." That earned Dean another punch on the shoulder, but Sam was smiling.

After Dean watched Sam and her friend enter the mall, he quickly pulled out his phone and sent Amy a text. He'd made a point to steal all of Sam's friends' phone numbers from her phone ever since she disappeared for a few days when she was eleven to go stay with a friend she'd made at school. After a few minutes his phone chirped with a reply from Amy. Dean grinned and drove toward the local bar to relieve some of its trust fund frat boy patrons of their money via pool.

\-------

The next few weeks leading up to prom were tense to say the least. John and Sam could barely be in the same room without sniping at each other about something or other. The day of prom, Sam came home in a particularly foul mood. She’d spent all day at school hearing the other students go on and on about prom, and about half the girls in her grade had been excused from school by their parents to go get their hair and makeup done. Even Amy had left two periods early after a quick apology and guilty look. It was a recipe for disaster.

An hour after Sam got home from school, the tension had gotten so volatile, Dean felt the need to intervene before it ignited into something everyone would regret. “Hey Sammy! Why don’t we leave Dad to his research and you and I go grab some grub? I’ll throw in one of those yogurt parfait things you like, my treat.” He gave Sam a look to indicate this was not up for debate. Sam gave Dean one of her bitchiest faces, but grabbed her coat anyway. John merely grunted and went back to his books, figuring the next job more important than if his kids went to get dinner together.

After about five minutes of driving, it became clear they were not going towards their usual dining spots, and Sam was becoming increasingly suspicious. “Where are we going Dean?”

“What? A guy can’t want to try something new? I heard about a new joint out this way. Humor me. They have rabbit food, don’t worry.”

Sam quieted with a glare and leaned back in her seat, staring at the view out the window as if it had personally offended her. She spoke up again when the Impala turned into the drive for a motel halfway across town from the one where they were staying. “Dean? What the hell is going on?” Sam hissed, not in the mood for one of Dean’s pranks.

“It’s a surprise Sammy!”

“Oh my god Dean, if you bought a hooker to try and make me feel better! So help me!”

Dean didn’t dignify that with a response and opened the door to the room. “Just get in.” He barked.

Sam debated obstinately refusing to go into the room before deciding to just go along with whatever hair-brained scheme Dean had concocted and strode into the room. She froze. Laying on one of the beds was a prom dress. _The_ prom dress. The one Amy had insisted Sam try on anyway after Sam’s gaze had drifted to it for the tenth time. It had fit perfectly, and walking out of the store without it was awful. The dress had consumed her thoughts for the whole week as everyone around her chatted about what they were wearing, and had made her mood even worse. Once she recovered from her shock enough to look around the rest of the room, she noticed there were matching kitten heel shoes on the floor, a slew of makeup, and an orchid corsage on the nightstand.

“Dean?” Sam’s voice was shaky. Dean briefly hugged her from behind, his chin no longer able to comfortably fit on her shoulder like it did when they were kids, and then strode purposefully into the room, grin plastered on his face.

“Happy prom night Sammy!”

“Dean... how did you…holy crap you didn’t steal these did you?” Sam asked suddenly in a panic.

“Whoah! Calm down! It’s all bought and paid for. Geez, I’m not a thief!”

“The years of credit card fraud say otherwise.” Sam jabbed back, but her gaze was locked on the dress. “How did you afford this?” She asked, finally turning to look at him.

Dean shrugged. “Rich kids going to college on mommy and daddy’s dime that suck at pool. Trust me, it’s fine. They won’t miss it. Now stop worrying and go shower or whatever so we can get this show on the road!” He waved her in the direction of the bathroom.

Sam re-entered the room from showering wearing her pants and button down, hair still damp. She placed her folded t-shirt, socks, and shoes in a neat pile on the bed before self consciously fingering her short hair while her gaze drifted once more to the dress. She’d always wanted long hair, but John had insisted she keep it short since long hair was a "safety hazard." Dean secretly suspected it was because John was afraid Sam would look too much like Mary if she grew her hair out.

Dean pulled his tub of styling paste out of his jacket pocket and handed it to Sam, startling her out of her thoughts. “Use this to spike your hair like you did for that dance you snuck out to a few years ago. It was cute.”

Sam’s eyes widened at the proffered tub. “You’re letting me use _this_ stuff? The ‘if I ever catch you using it I will skin you alive because it’s damn expensive and it won’t save your mop do don’t even try it’ stuff?”

Dean gave Sam a mock glare. “Yea, well, special occasion and all that. But this is a one time deal! After tonight you keep your paws off it, capisce?”

Sam grinned and snatched the tub out of Dean’s hands, made a beeline for the bathroom, and slammed the door. The sounds of a blow-dryer could be heard moments later and Dean grinned to himself even while lamenting how little of it would be left for him to use in the morning.

He walked over to the nightstand to consider the makeup he’d gotten for Sam. The woman who had rescued him when he’d been staring hopelessly lost at the selection at CVS had assured him these colors would match Sam’s palette and dress based on the pictures Dean showed her. He laid all the supplies out in a methodical fashion, going over in his brain what he was supposed to do with it. He’d learned a little from this chick named Karen he’d dated a few years back. She’d been attending cosmetology school and needed someone to practice on, and well, she was really freaking hot, and after the panties thing in high school how bad could it be? One thing led to another and Dean had acquired a basic knowledge of how the hell this stuff was supposed to go on a face.

This turned out to be as beneficial as he’d supposed when Sam looked helplessly at his selection. “Dean, I have no idea how to put this stuff on.” She confessed awkwardly. “I never really had friends who used it, and you know Dad’s opinion of the stuff.”

“Well it’s just your luck that your brother banged a girl in makeup school a few years back.” Dean said with a sly grin and an eyebrow waggle.

“Gross! Dean! There’s a thing called over-sharing! And knowledge does not get transferred via coitus!” Sam protested warily as Dean gestured for her to sit on the bed.

“Sit down and shut up. Trust me for once will ya?”

Sam did so, and closed her eyes with a great deal of apprehension as Dean began applying foundation. It became quickly apparent that Dean had some idea what he was doing, and Sam was burning with curiosity as to how. She was sure she’d have found out by now if Dean was secretly cross dressing in the night or something, but she kept her mouth shut and let him work.

After about half an hour, a few “fuck! Wait! Don’t panic! I can fix it!”s followed by removal and re-application of makeup, Dean proclaimed Sam a “classy dame” and “not at all a whore.” Sam rolled her eyes and went to go look in the bathroom mirror to make sure Dean hadn’t decided to troll her and make her look like a clown or something, and gasped when she saw her reflection. She’d never looked this feminine in her life. The back and ends of her hair were spiked out in a cute punk style, her lips a subdued shade just a touch pinker than her normal color, and her eyes were smoky. Any desire to know where the hell Dean had learned to do this flew out the window in the wake of overwhelming gratitude and joy. She had never felt this beautiful before. This normal.

Dean was waiting awkwardly, trying not to show that he was nervous about Sam’s reaction, when she threw herself into him, almost knocking him to the ground. “Thank you.” She hugged him quickly and dashed off to change into the rest of the outfit. Dean blinked, shell shocked from the whirlwind of Sam finally getting excited and laughed. When Sam finally emerged from the bathroom, Dean’s eyes widened in shock. He couldn’t remember the last time he’d seen Sam in a skirt, let alone a dress. She looked amazing – beautiful really, and very grown up.

“Nope. Changed my mind. You can’t go. You’ll rip the crap out of it from beating off the boys with a stick! And I didn’t go to all this trouble for you to start a brawl.” Dean proclaimed with a grin, pleased that he’d actually done a pretty decent job with Sam’s makeup.

Sam laughed and rolled her eyes at him, then stopped. “Wait, you got a ticket too?”

Dean looked at her confused. “What the hell did you think all this was for?”

“I dunno. Pity dress up?” Sam confessed to the ground as she awkwardly smoothed an invisible wrinkle on her skirt.

“Like I would blow money on pity dress up, regardless of how fun it is to school frat boys in pool. Course I got you a ticket. Well, Amy did, but I gave her the cash, so…”

“So that was how you found out about the dress!” Realization dawned. “You stole her number out of my phone didn’t you? You jerk!” Sam’s outrage was robbed of venom as her reflection in the motel’s full-length mirror kept catching her attention.

Dean smiled and silently let her have a moment to admire herself before coughing to draw her attention back to him. “Whatever. Anyway, she’s meeting us outside the venue soon, so we should head out.” Dean picked up the corsage box and opened it, fastening the flower to Sam’s wrist. “Don’t want to keep my lovely co-conspirator waiting.”

Sam rolled her eyes, “I should never have told you Amy thought you were hot,” but her smile was beaming with excitement. She leaned over and gave Dean a hug.

"Damn, knew I shouldn't have bought you heels you amazon" he complained, but returned the hug anyway.

Half an hour later, the Impala slowed to a stop in front of some ritzy hotel. Amy was chatting with the doorman as she waited outside. Sam practically lept out of the car. “Slow down there sasquatch. Here.” Dean tossed her the room key for the motel. “I booked it for the night if you decide to engage in the age old tradition of prom night cherry popping.”

Sam made a face and shoved him. “Ugh! Dean! You are such a perv!” but she did take the key, and Dean gave her a knowing look.

“Whatever, just call me when you wanna leave if you don’t arrange for other transportation. Either way, I told Dad you were having an anti-prom slumber party with some friends from school, so if you change back at the motel he never has to know.”

Sam blinked rapidly to prevent herself from crying as she slid across the front bench and pulled Dean into a bear hug. “Thank you.” She whispered into his ear.

He hugged her tightly before pulling away. “Hey, don’t want to mess up your dress. And you know the rule about chick-flick moments. Go on, get out of the car so I can leave before this ass hole limo driver behind me has an aneurism.” He leaned out of the driver’s seat window. “I’m dropping someone off you goddamn douchebag! The rich assholes in your back seat aren’t the only ones going ya know!” He pulled back into the car after flipping the guy the bird only to see Sam was already out of the car and running towards her friend. The two hugged and chatted excitedly. Dean smiled, he’d never seen Sam look so happy before. Sam quickly turned and waved goodbye to Dean before heading inside. Dean had just started to wave back when the limo honked loudly, wiping the grin of a plan well executed off his face. “ALL RIGHT I’M GOING!” he put the Impala in gear. “Freaking limos.”

**Author's Note:**

> I know in the show Dean sees Sam going to Stanford as a rejection and betrayal of the family. However, Sam is a girl in this fic, so I thought that might change things. Dean initially tried to discourage Joe and Krissy from hunting in the show, and I see Dean as being a little old fashioned in some ways, so I figured he might be less thrilled about Sam joining the family business and more supportive of Stanford if Sam were a girl.


End file.
